Cheveldayoff left the Grizzlies in 1997 to become the general manager of the Chicago Wolves, also of the IHL. The Wolves won two Turner Cups under Cheveldayoff. After the demise of the IHL in 2001, the Wolves were absorbed into the American Hockey League and, in their first season, won the Calder Cup as AHL champions. They won a second AHL championship in 2007-08.

National Hockey League

The Chicago Blackhawks hired Cheveldayoff as their assistant general manager for the 2009-2010 season, working under general manager Stan Bowman. In his first season with the Hawks, the team won the Stanley Cup, defeating the Philadelphia Flyers in six games. Cheveldayoff spent two seasons with the Hawks.